US941088A - Azo dye and process of making same. - Google Patents

Azo dye and process of making same. Download PDF

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Publication number
US941088A
US941088A US48065109A US1909480651A US941088A US 941088 A US941088 A US 941088A US 48065109 A US48065109 A US 48065109A US 1909480651 A US1909480651 A US 1909480651A US 941088 A US941088 A US 941088A
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Prior art keywords
azo dye
making same
acid
red
hours
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Expired - Lifetime
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US48065109A
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Carl Oskar Mueller
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Hoechst AG
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Hoechst AG
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Priority to US48065109A priority Critical patent/US941088A/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/08—Preparation of azo dyes from other azo compounds by reduction

Definitions

  • CARL OSKAR MULLER OF HOCHST-ON-T HE-MAIN, G ERMANY, ASSIGNOR TO FARE- VVERKE VORM. :MEISTER LUCIUS & BRUNING, OF HOCI-IST-ON-THE-MAIN, GERMANY,
  • Example I 25 kg. of p-nitrobenZoyl-pphenylenediamin of the formula:
  • Example 11 25.7 kg. of p-nitrobenzoyl- Specification of Letters Patent.
  • m-phenylene-diamin are heated in about 200 liters of water and 72 kg. of hydrochloric acid of 80% strength, for about 3 hours, to 60 and well stirred. After having "cooled to 10, a solution of 8 kg. of nitrite is allowed to run into about 20 liters and this mixture is then stirred for about 1!; hours until no unchanged base can be traced any more.
  • the diazo compound thus formed is filtered and run into a solution of 40 kg. of p-nitrobenzoyl 2.5.7 aminonaphtholsulfonic acid and 60 kg. of sodium carbonate in about 2000 liters of water. Thereupon the mass is stirred for 24 hours at 20, heated to and then 100 kg. of crystallized NI-LS added to it.
  • the stirring is continued for about 2 hours at 5560 when the formation of the dyestuff is terminated.
  • the dyestutf is then filtered off, pressed and dried. It dyes unmordanted cotton yellowishred tints, while its developments by means of betanaphthol also give yellowish-red tints.
  • R means an aryl residue,by combining dia'zotized mononitrobenzoylated diamins with acidylated 2.5.7-a1ninonaphtholsulfonic acids and reducing the nitro group.

Description

UNITED STATES PATENT OFFICE.
CARL OSKAR MULLER, OF HOCHST-ON-T HE-MAIN, G ERMANY, ASSIGNOR TO FARE- VVERKE VORM. :MEISTER LUCIUS & BRUNING, OF HOCI-IST-ON-THE-MAIN, GERMANY,
A CORPORATION OF GERMANY.
AZO DYE AND PROCESS OF MAKING SA'ME.
No Drawing.
To all whom it may concern:
Be it known that I, CARL OSKAR Mt'JLLnR, a citizen of the Empire of Germany, residing at l-Iochst-on-the-vlain, Germany, have invented certain new and useful Improvements in the Manufacture of New Dyestuffs, of which the following is a specification.
I have found that by combining diazotized mononitro-benzoylated diamins of the gen eral formula:
with 2.5.7-aminonaphtholsulfonic acid or a derivative thereof in which substitution has occurred in the amino group, and by treating the coloring matters thus formed with reducing agents suitable for transforming the nitro groups into the amino groups, substantive dyestuffs are obtained which can be diazotized on the fiber and combined with phenols or amins.
Example I: 25 kg. of p-nitrobenZoyl-pphenylenediamin of the formula:
are converted in known manner into the diazo compound and then combined with 83 kg. of acetyl-2.5.7 aminonaphtholsulfonic acid in solution alkaline with sodium carbonate. The formation of the dyestufi" is terminated after 2 hours. To this, kg. of crystallized sodium sulfid are added and the mixture is heated for about 21} hours to 60 C. until all the nitro-dyestuff has disappeared. The dyestuff which separates is filtered off and dried. It dyes unmordanted cotton bluish-red tints which by diazotization on the fiber and combination with betanaphthol, become faster to washing.
Example 11: 25.7 kg. of p-nitrobenzoyl- Specification of Letters Patent.
Application filed March 1, 1909.
Patented Nov. 23, 1909. Serial No. 480,651.
m-phenylene-diamin are heated in about 200 liters of water and 72 kg. of hydrochloric acid of 80% strength, for about 3 hours, to 60 and well stirred. After having "cooled to 10, a solution of 8 kg. of nitrite is allowed to run into about 20 liters and this mixture is then stirred for about 1!; hours until no unchanged base can be traced any more. The diazo compound thus formed is filtered and run into a solution of 40 kg. of p-nitrobenzoyl 2.5.7 aminonaphtholsulfonic acid and 60 kg. of sodium carbonate in about 2000 liters of water. Thereupon the mass is stirred for 24 hours at 20, heated to and then 100 kg. of crystallized NI-LS added to it. The stirring is continued for about 2 hours at 5560 when the formation of the dyestuff is terminated. The dyestutf is then filtered off, pressed and dried. It dyes unmordanted cotton yellowishred tints, while its developments by means of betanaphthol also give yellowish-red tints.
Having now described my invention what I claim is:
1. The herein described process for manufacturing red dyestuffs of the general formula uncoo rnnn Ng acidyl-2.5.7-amin0naphtholsulfonic acid,
wherein R means an aryl residue,by combining dia'zotized mononitrobenzoylated diamins with acidylated 2.5.7-a1ninonaphtholsulfonic acids and reducing the nitro group.
2. The herein described process for manufacturing red dyestuffs of the formula:
\/ N aminobenz0yl-2.5.7-aminonap11tl1o1su1fonic acid,
by combining mono-nitrobenzoylated metaphenylenediamin with nitroarylacidyl-2.5.7- aminonaphtholsulfonic acids and reducing the nitro-group.
3. As new products, the dyestuffs 0f the when treated with beta-naphthol, red dyegeneral formula: ings. 10
/NH.CO.C8H4 NH2 In testimony whereof, I afiix my signature N acidy1-2.5.7-amin0naphtholsulfonic acid, 111 plesence being green powders with a metallic luster, Vitnesses:
which are soluble in hot water with a red JEAN GRUND,
c0101, dyeing cotton red tints and giving, CARL GRUND.
US48065109A 1909-03-01 1909-03-01 Azo dye and process of making same. Expired - Lifetime US941088A (en)

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